Process of preparing aliphatic sulpho-ethers



Patented Dec. 1, 1936 2,062,957

UITE STATES PATENT OFFICE PROCESS OF PREPARING ALIPHATIC SULPHO-ETHERS Alfred William Baldwin, Ashton-on-Mersey, and

Anthony James Hailwood, Altrincham, En,- land, assignors to imperial Chemical Industries Limited, a corporation of Great Britain No Drawing. Application May 6, 1932, Serial No. 609,768. In Great Britain May 16, 1931 1 Claim. (Cl. 260-151) This invention relates to chemical compounds, illustrate some of the products falling within the more particularly substances exhibiting in a proinvention and how they may be prepared. nounced degree the properties of wetting, deter- E a l I gent, foaming and dispersive agents, and a procmp e ess for the manufacture thereof. Nine and one-half parts of dodecyl alcohol are As is well known, ordinary wetting agents and dissolved in 50 parts of xylene and the solution is detergents such as soaps, i. e., the alkali metal boiled under reflux with 2.3 parts of finely ground salts of the fatty acids, are of little or no value sodamide until ammonia ceases to be evolved. for use in acidic solutions because the water-sol- Twelve parts of sodium B-bromoethanesulpho- 1o lble alkali metal salts are converted into the wanate, in a finely divided state, is added and re- 10 ter-insoluble fatty acids. Furthermore, soaps fiuxing is continued with vigorous agitation for are precipitated in hard water by salts of calcihours. The xylene is then removed by distilum, magnesium and the like. lation under reduced pressure. The residue is a It is an object of the present invention to prostifi pasty mass. It is freely soluble in water and 15 duce new substances which possess wetting, demay be freed from impurities if desired by dis- 15 tergent, foaming and dispersive properties in acid solving in water and salting out. solutions and hard water. A further object is the Example H production of compounds which do not suffer decomposition by the action of hydrolytic agencies. Twelve and one-tenth parts of cetyl alcohol A still further object is the provision of a new are dissolved in 50 parts of xylene and the solu- L0 and improved process for producing products of tion is boiled under reflux with 2.3 parts of finely the character above described. Other objects will ground sodamide until ammonia ceases to be appear hereinafter. evolved. Twelve parts of sodium B-bromo- These objects are accomplished according to ethane sulphonate, in a finely divided state, are

W the present invention by combining a long chain added and refluxing is continued with vigorous saturated or unsaturated aliphatic radical and a agitation for 15 hours. The xylene is then re- B-sulphoethyl group by means of an ether link moved by distillation under reduced pressure. to produce compounds having the general for- The residue resembles that of Example I and the mulae product is purified, if desired, in a similar way.

I R-O--CH2(-)r-CH2-SO3H Example In 30 II R--0--CH --CH2-SO3M Thirteen and four-tenths parts of oleyl alcohol are dissolved in 50 parts of xylene and the solution is boiled under reflux with 2.3 parts of finely ground sodamide until ammonia ceases to be evolved. Twelve parts of sodium B-bromoethanesulphonate, in a finely divided state, is added and refluxing is continued with vigorous agitation for 15 hours. The xylene is then removed by distillation under reduced pressure. 40 wherein R and M have the foregoing significa- The residue resembles that of Example I and is tion, with an alkali metal B-halogen-ethanesulsimilarly treated. phonate, the resultant product being the alkali A similar compound is obtained when instead metal salt of the sulpho-acid represented by Forof 13.4 parts of oleyl alcohol, 13.5 parts of octamula II. The reaction is preferably effected in a decyl alcohol is used. Instead of sodium 3- 45 solvent or suspension medium. The free sulphobromo ethanesulphonate, sodium B chloro acid may be formed from its alkali metal salt in ethanesulphonate may be employed. any suitable manner, e. g., by treatment with a di- It will be understood that the invention is not lute mineral acid. limited by the above examples. The products While the invention is susceptible of considermay be any compounds having the general forable variation and modification in the manner of mula its practical application, particularly as regards the nature and proportions of materials employed In R O CH2 CH2 803x in which R represents a long chain, saturated or unsaturated aliphatic radical containing not less 35 than six carbon atoms and M represents an alkali metal. The process of the invention may be carried out by reacting an alkali metal alkoxide having the formula and the exact method of procedure, the following in which R. represents a saturated or unsaturated examples, in which the parts are by weight, will aliphatic radical containing at least six carbon 55 atoms and X represents hydrogen or an alkali metal (preferably potassium or sodium). The radical B may have a straight or branched chain. In general, it is preferable that R be a long chain, saturated or unsaturated alkyl radical containing more than about ten carbon atoms such as, for example, dodecyl, c'etyl, oleyl, and the like radicals.

The aliphatic alcohols employed as starting materials in accordancewith the process of "the invention may be those contained in wool-fat, or those obtained from other natural sources, e. g., stearyl alcohol (octadecyl alcohol) ,cetyl alcohol (hexadecyl alcohol), ceryl alcohol and myricyl alcohol. They'may also be such, e. g.,' dode'cyl alcohol (lauryl alcohol) as are now obtainable by reduction of esters of I acids. Synthetic-higher alcohols, for-example, those obtained by the hydrogenation of carbon oxides under elevated temperaturesand pressures may also be employed. The process "islikewise applicable to the treatment of 'mixtures of anyof the foregoing alcohols, e. -g., complex mixtures of synthetic alcohols-boiling above aboutl60 C. and, jin jgeneral, to the treatment of any alcohols con- :taining six or morecarbon atoms.

' will be apparent by the foregoing description "ofthe products with reference to Formula III,

the alcohols preferably employed are the aliphatic monohydric alcohols of'the saturated s'eries con- "taining ten orin'ore carbon atoms'such as, for

examplefdodecyl alcohol, cetyl alcohol, octadecyl 1' alcohol and myricyl alcoholgor of the unsaturated "series, such as, forexample, linalooLgeraniol and oleyl-alcoholf I It is preferable, furthermore, to employ primary, straight chain alcohols. When alcohols having branched chains are employed,

the side chains should preferably be relatively short.

As previously indicated, a' 's'olvent 'or suspension medium'inay be employed in effecting thereaction; -By a solvent or suspension medium is meant any liquid which is inert to the reactants and products'or does not affect the reaction unfavorably. As examples 'of'such'solvent or susthe corresponding "fatty pension media, we may mention xylene and toluene.

The temperature employed in carrying out the reaction between the alkali metal alkoxide and the alkali metal B-halogenethanesulphonate may vary within relatively Wide limits but in any case should be below the temperature giving rise to decomposition of the products.

The products, viz., the sulpho-acids and alkali metal salts thereof, possess remarkable soap-like properties, are stable to acids and can be used in calcareous or other hard water. Further, they do not'suffer'decomposition by the action of hydrolyt'ic agencies. It will be understood, of course, that the various products may differ as regards certain characteristics. For instance, the products 'o'f-all the examples have pronounced soaplike properties but difier in other respects. Thus,

the product of Example I is a wetting agent but its detergent power is relatively low. The prod- -ucts*of Examples 11 and III, on the other hand,

"in the following claims.

We claim:

The process which comprises reacting an allphatic alcohol containing at least six carbon atoms with sodamide in the presence of an alkylated benzene, and heating the resultant solvent reaction mixture with a sodium beta-halogene'thane-sulphonate.

ALFRED WILLIAM BALDWIN. ANTHONY JAMES HAILWOOD. 

